Though Boston is small, heading into the city can feel overwhelming. We’ve created itineraries that break down four of Boston’s most popular locations to make your stay as easy as possible. Fortunately, Boston is quick and easy to navigate, so these suggestions are interchangeable.
Happy stay-cay!
Back Bay
Start the day with coffee and breakfast at independent bookstore Trident Booksellers and Cafe. You’ll need the energy for a stroll down Newbury Street, which is home to upscale restaurants, shops and galleries.
For art lovers, Vose Galleries is one of the oldest fine art galleries in the country, and the Copley Society of Art features all manner of artworks by local artists. Along the way, you’ll find plenty of shopping. And don’t miss the Boston Public Library, renowned for its historical significance and architecture.
For lunch, choose from one of the many restaurants and counters within Eataly in the Prudential Center. Then head up (literally), to the Prudential Skywalk Tour for a 360 view of the city.
Did you know you can take a tour of Fenway Park? Even if you’re not a sports enthusiast, historical Fenway is one of the country’s most beloved ballparks and worth getting to know better. Tours are offered year-round; see website for details.
If you’re a lover of the symphony, you can take a tour of Boston Symphony Hall, home to the Boston Symphony Orchestra and the Boston Pops. While you’re at it, see what’s happening at Berklee Performance Center at Berklee College of Music. Other can’t-miss cultural stops include the Museum of Fine Arts and the Isabella Stewart Gardner Museum.
Where to stay: The Hilton Boston Back Bay is a AAA Three Diamond Rated hotel right in the middle of all the action, making it simple to hit the town.
Faneuil Hall
Waste no time and walk right over to Faneuil Hall Marketplace in the historic Quincy Market building for a bite to eat, something to drink or some shopping. Boasting 18 restaurants and 35 colonnade eateries, you can find pretty much anything here, from local clam chowder to sushi to enchiladas. Shop for gifts such as local art, unique jewelry or fun Boston souvenirs for family and friends at the numerous outdoor canopy shops.
From Faneuil Hall, you can book a tour of Boston’s famous Freedom Trail, or take your own. You can’t miss it – the 2.5-mile trail through the city is marked with painted red lines along the sidewalks. Either way, you are going to work up an appetite for some good New England eating. Luckily, Boston’s seafood institution the Union Oyster House is located right along the Freedom Trail, where you can eat oysters to your heart’s content. While you wait for a table, cross the street and check out the New England Holocaust Memorial, a modern installment of six 54-foot glass towers dedicated to Holocaust victims.
Check out the nearby Boston Waterfront, where you can tour the world-famous New England Aquarium. At the aquarium you can book a whale watching excursion through Boston Harbor Cruises, weather permitting, that takes you to Cape Cod Bay’s marine sanctuary Stellwagen Bank. For a more historic cruise, hop aboard “Old Ironsides,” the 1797 navy ship USS Constitution.
As you head back to the present, be sure to visit the Seaport District, Boston’s hottest new neighborhood, with plenty of options for dinner.
Where to stay: For style and convenience, stay at the Hilton Downtown Boston Faneuil Hall. This AAA Four Diamond Rated hotel, built in 1928, is pet-friendly and was Boston’s first art deco style skyscraper.
North End
The North End is world-renowned for its authentic Italian restaurants. The first (or last!) thing you have to do is stop for coffee and cannoli. Touted as Boston’s first Italian café, Caffe Vittoria serves up top-notch cappuccino and pastries in a sublimely Italian ambiance.
For lunch, the choice is yours – authentic Italian sub or pizza? For a huge slice of old world-style pizza, Ernesto’s can’t be beat. If a good sandwich is what you are after, check out Monica’s Mercato & Salumeria, a North End institution serving up what some say are the best subs in the city.
You’ll probably need to walk it off afterwards, so take a stroll down the North End’s many quirky and winding streets. Take in some history at Paul Revere’s House and the Old North Church, from where Revere began his famous midnight ride.
For an elegant North End dinner, Lucca features locally-sourced seafood, pasta and a 500-selection wine list. If you prefer something more casual, try Al Dente or Panza; both serve up classic pasta dishes with a laid back and bustling vibe.
Where to stay: Within close proximity to the delicious foods of Boston’s North End, Ames Boston Hotel Curio Collection by Hilton is a contemporary chic luxury boutique hotel set in Boston’s first sky scraper, built from 1893-1915.
Theater District
For those who love theater, Boston doesn’t disappoint. Boston’s Theater District boasts at least ten world-famous theaters, including the Wang, the Shubert, and Boston Opera House, home to the Boston Ballet’s Nutcracker Suite. Check out the Blue Man Group at Charles Playhouse!
While you’re exploring, grab a coffee (or a glass of wine, or a beer) at the trendy Jaho Coffee Roasters. Options abound for dinner, either before or after a show. For seafood, Legal Crossing, a branch of Legal Seafoods, is situated close to the Opera House and Emerson College’s Paramount Theater. Craving some sushi? Check out Fin’s, situated near Emerson’s other two theaters, the Colonial and the Cutler Majestic.
Where to stay: Check in at the AAA Three Diamond Rated DoubleTree by Hilton Boston Downtown, which boasts a modern feng shui vibe and an Olympic-size pool.
What’s your ideal Boston staycation? Tell us in the comments.
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